Asciano holiday lettings

We found 2,458 holiday rentals — enter your dates for availability

Discover a selection of 23 homes, 23 apartments and other holiday rentals in Asciano that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, including Wi-Fi and parking. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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Head to the relaxing city of Asciano

Enjoy the wineries and other features of Asciano. This relaxing city attracts visitors thanks to its cheese shops and coffee shops. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Asciano

Are you looking for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Asciano a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • San Giovanni Terme Rapolano (3.6 mi / 5.8 km)
  • Terme Antica Querciolaia (4.7 mi / 7.5 km)
  • Siena Circuit (6.8 mi / 10.9 km)
  • Villa a Sesta Polo Club (10.6 mi / 17.1 km)
  • Castiglion del Bosco Winery (12.9 mi / 20.7 km)
  • Tenuta Greppo Franco Biondi Santi (13.4 mi / 21.6 km)

Exploring the natural features in Asciano

Whether you're an adventurous traveller or just want to take in the scenery, Asciano is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Terme Antica Querciolaia (4.7 mi / 7.5 km)
  • Horti Leonini (12.3 mi / 19.8 km)
  • Historic Centre of Pienza (12.4 mi / 19.9 km)
  • Chianti Sculpture Park (14.2 mi / 22.9 km)
  • Terme di Montepulciano Spa (16.5 mi / 26.5 km)
  • Val di Chiana (16.7 mi / 26.9 km)

Travelling to and around Asciano

The nearest airport is in Peretola Airport (FLR), located 43.2 mi (69.5 km) from the city centre.

If you prefer to travel by train, Asciano Monte Oliveto Maggiore Station, Asciano Station and Castelnuovo Berardenga Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Asciano when booking a holiday rental?
When considering a holiday rental in Asciano, Tuscany, a popular area to stay is the charming historic centre. This area offers a delightful blend of local culture and stunning architecture, making it an ideal base for your Tuscan adventure. You'll find a variety of properties, from rustic villas to quaint apartments, providing ample options to suit different preferences.

Staying in the historic centre allows easy access to attractions such as the beautiful Church of San Francesco, known for its remarkable frescoes, and the nearby Abbey of Monte Oliveto Maggiore, a captivating monastery surrounded by idyllic countryside. The vibrant piazzas and local restaurants also offer a fantastic opportunity to savour authentic Tuscan cuisine and immerse yourself in the region's rich heritage.

Another noteworthy area is the surrounding countryside, dotted with charming farmhouses and villas. This setting provides a serene escape, with breathtaking views of the rolling hills and vineyards. Guests can enjoy outdoor activities such as hiking or cycling, with numerous trails that showcase the stunning landscape.
How much does it cost to rent a holiday home in Asciano?
Prices for holiday rentals in Asciano vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Asciano to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Asciano holiday house rentals?
You can find great discounts on house rentals in Asciano on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Asciano?
In Asciano, holiday houses are the most popular type of holiday rental, with around 184 available throughout the picturesque Tuscan countryside. These spacious properties typically feature multiple bedrooms, fully equipped kitchens, and outdoor areas where guests can enjoy alfresco dining while taking in the stunning views of the rolling hills. Many of these houses are located near top attractions such as the Crete Senesi and the charming medieval town centre.

Apartments are also quite common, with about 180 options scattered across the area. These rentals often provide a more intimate setting, complete with modern amenities like Wi-Fi, comfortable living spaces, and kitchens for self-catering. For those seeking a more luxurious experience, approximately 76 villas are available, offering upscale amenities such as private pools and expansive gardens.

Cottages, though fewer in number at about 12, provide a quaint and rustic retreat for visitors wanting a traditional Tuscan experience.
Are there any family house rentals in Asciano?
In Asciano, Tuscany, there are a variety of family-friendly holiday rentals available, with around 46 options throughout the area. This charming town is situated amidst the beautiful landscapes of the Crete Senesi, making it an excellent base for families seeking a mix of relaxation and adventure. Many properties boast spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Visitors can enjoy amenities such as private gardens, barbecues, and sometimes even swimming pools, superb for unwinding after a day of sightseeing. Asciano is well-positioned for exploring nearby attractions like the stunning towns of Siena and Montalcino, known for their rich history and exquisite local cuisine.
Can I rent a holiday home with a pool or hot tub in Asciano?
In Asciano, Tuscany, there are plenty of holiday homes available for rent that feature pools or hot tubs, with around 91 options to choose from. This picturesque town, located in the beautiful Crete Senesi region, offers a tranquil setting for travellers seeking relaxation. Many of these properties come with private swimming pools, ideal for cooling off during the warm Tuscan summers, while some rentals may also include hot tubs for a more luxurious experience.

Visitors can expect a range of amenities, including spacious outdoor areas for sunbathing, fully equipped kitchens for preparing local cuisine, and comfortable living spaces that highlight the region's rustic charm. Additionally, many homes offer stunning views of the surrounding countryside, enhancing the overall appeal of a holiday in this enchanting part of Italy.
Can I find long-stay holiday rentals in Asciano?
A long-stay holiday rental in Asciano is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Asciano?
In Asciano, Tuscany, there are numerous pet-friendly house rentals available, allowing travellers to fully enjoy their stay without leaving their furry friends behind. The area is characterised by its stunning landscapes, rolling hills, and charming medieval architecture, providing a picturesque backdrop for a holiday. Many of the holiday rentals come equipped with amenities such as private gardens, terraces, and fully equipped kitchens, ensuring a comfortable and convenient stay for families or groups.

The nearby Val d'Orcia region, a UNESCO World Heritage site, offers a wealth of outdoor activities, including scenic walks and hiking trails that you and your pets can enjoy together. There are also local pet-friendly cafés and restaurants, which enhance the experience for travellers with pets.
Are there any remote work holiday rentals in Asciano?
In Asciano, Tuscany, there are numerous remote work-friendly holiday rentals available, with around 408 options to choose from. This picturesque village is renowned for its stunning landscapes and historic charm, making it an ideal place for those looking to blend work and leisure. Many properties provide essential amenities such as high-speed Wi-Fi and dedicated workspaces, ensuring a productive environment while enjoying the beautiful surroundings.

Travellers can expect a variety of accommodations, from charming rustic villas to modern apartments, often featuring well-equipped kitchens, spacious living areas, and outdoor spaces to relax in after a day of work. Asciano's proximity to attractions like the stunning Crete Senesi and the historic city of Siena offers ample opportunities for exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Asciano holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Asciano with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Asciano?
In Asciano, popular rental amenities include kitchens, which allow guests to prepare their own meals using local ingredients. Many properties also feature fireplaces, adding a cosy touch to the accommodations, especially during cooler evenings. Onsite parking is commonly available, making it convenient for those travelling by car. For pet owners, several rentals permit pets, ensuring that furry companions can join the trip. Additionally, coffee and tea makers are often provided, allowing guests to enjoy a warm beverage at their leisure.
When is the best time to visit Asciano for a holiday rental?
The best time to visit Asciano for a holiday rental is during the enchanting month of October, when the region showcases its stunning autumn colours and mild climate. This period falls within the peak season, which spans from August to October, attracting travellers keen to explore the beautiful landscapes of Tuscany.

In October, temperatures in Asciano typically range from 10 to 20 degrees Celsius, creating a comfortable environment for outdoor activities such as hiking, cycling, and leisurely strolls through the picturesque countryside. The charming hilltop town allows for easy access to nearby vineyards and olive groves, where you can savour local flavours and immerse yourself in the Tuscan lifestyle.

For those seeking a more budget-friendly option, January presents a quieter alternative. While it's the low season, visitors can still enjoy the serene beauty of the landscape and have a more intimate experience without the crowds—great for unwinding and appreciating the tranquil atmosphere.

Ultimately, whether you prefer the vibrant energy of October with its harvest festivals and cultural events or the peacefulness of January, Asciano offers a unique charm year-round.
How early should I book a Asciano holiday rental?
Book your Asciano holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Asciano?
In Asciano, visitors can experience firsthand the stunning landscapes of the Tuscan countryside, which are characterised by rolling hills and picturesque vineyards. The town itself boasts historical attractions such as the beautiful Church of San Giovanni Battista, known for its striking frescoes. The surrounding area is rich in natural beauty, making it ideal for outdoor activities like hiking and cycling.

Just a short distance away, the famous Crete Senesi region offers unique geological features and breathtaking views, superb for those seeking a tranquil escape. Additionally, the nearby Abbey of Monte Oliveto Maggiore, set within a serene setting, is a must-visit for its impressive architecture and beautiful frescoes.

For those interested in local cuisine, Asciano is surrounded by traditional farms and vineyards, providing opportunities to sample authentic Tuscan wines and dishes.
Can I change or cancel my Asciano home rental booking on Vrbo?
To find Asciano holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Asciano holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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